Sodium Hydroxide → 6-(3-Amino-4-methylphenyl)-3-(3,4,5-trimethoxyphenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole

HRID 15026Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 15026
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]3=[N:13][N:14]=[C:15]([C:16]4[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=4)[N:10]3[N:9]=2)=[CH:4][C:3]=1[N+:28]([O-])=O.[Sn](Cl)Cl.[OH-].[Na+]>CO.O>[NH2:28][C:3]1[CH:4]=[C:5]([C:8]2[S:12][C:11]3=[N:13][N:14]=[C:15]([C:16]4[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=4)[N:10]3[N:9]=2)[CH:6]=[CH:7][C:2]=1[CH3:1]

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 249548716-(4-Methyl-3-nitrophenyl)-3-(3,4,5-trimethoxyphenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole

Produkt 1

HCID 249545036-(3-Amino-4-methylphenyl)-3-(3,4,5-trimethoxyphenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoleAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 6-(4-methyl-3-nitrophenyl)-3-(3,4,5-trimethoxyphenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole (256 mg, 0.6 mmol) and tin(II) chloride (675 mg, 3 mmol) in methanol (25 mL) was refluxed under argon for 6 h. It was then diluted with water (30 mL) and neutralized with 2N aqueous sodium hydroxide to pH=12, and extracted with ethyl acetate (3×20 mL). The extracts were dried, concentrated and the residue was purified by column chromatography (EtOAc as eluent) to give 66 mg (28%) of the title compound as solid. 1H NMR (CDCl3): 7.71 (s, 2H), 7.23 (m, 2H), 7.17 (s, 1H), 4.00 (s, 6H), 3.94 (s, 3H), 2.26 (s, 3H).

Aufarbeitung

  1. temperaturewas refluxed under argon for 6 h
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. customThe extracts were dried
  4. concentrationconcentrated
  5. customthe residue was purified by column chromatography (EtOAc as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-cb8d063aca674e9090bef4a28ee8282c
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732468B2

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